Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites

被引:84
作者
Kakeya, H
Onose, R
Koshino, H
Yoshida, A
Kobayashi, K
Kageyama, S
Osada, H
机构
[1] RIKEN, Antibiot Lab, Wako, Saitama 3510198, Japan
[2] RIKEN, Characterizat Ctr, Wako, Saitama 3510198, Japan
关键词
D O I
10.1021/ja0127279
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A unique pentaketide dimer structure of a novel fungal metabolite with antiangiogenic activity, designated as epoxyquinol A (1), was determined on the basis of NMR spectral data as well as the X-ray crystallographic analysis. 1 inhibits the endothelial migration induced by vascular endothelial growth factor (ED100 = 3 μg/mL). Copyright © 2002 American Chemical Society.
引用
收藏
页码:3496 / 3497
页数:2
相关论文
共 16 条
[1]   Mechanisms of angiogenesis and arteriogenesis [J].
Carmeliet, P .
NATURE MEDICINE, 2000, 6 (04) :389-395
[2]   THALIDOMIDE IS AN INHIBITOR OF ANGIOGENESIS [J].
DAMATO, RJ ;
LOUGHNAN, MS ;
FLYNN, E ;
FOLKMAN, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (09) :4082-4085
[3]   Metabolites of the higher fungi.: Part 32.: Rosnecatrone, a phytotoxic bicyclo[4.1.0]hept-3-en-2-one from the fungus Rosellinia necatrix Prill [J].
Edwards, RL ;
Maitland, DJ ;
Scowen, IJ ;
De Sousa, AJT ;
Whalley, AJS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (05) :537-542
[4]   CONTROLLING THE VASCULATURE - ANGIOGENESIS, ANTI-ANGIOGENESIS AND VASCULAR TARGETING OF GENE-THERAPY [J].
FAN, TPD ;
JAGGAR, R ;
BICKNELL, R .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1995, 16 (02) :57-66
[5]   WHAT IS THE EVIDENCE THAT TUMORS ARE ANGIOGENESIS DEPENDENT [J].
FOLKMAN, J .
JNCI-JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1990, 82 (01) :4-6
[6]   LONGITHORONE-A - UNPRECEDENTED DIMERIC PRENYLATED QUINONE FROM THE TUNICATE APLYDIUM-LONGITHORAX [J].
FU, X ;
HOSSAIN, MB ;
VANDERHELM, D ;
SCHMITZ, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12125-12126
[7]   The rationale and future potential of angiogenesis inhibitors in neoplasia [J].
Gasparini, G .
DRUGS, 1999, 58 (01) :17-38
[8]   Exploring chemical diversity of epoxyquinoid natural products: Synthesis and biological activity of (-)-jesterone and related molecules [J].
Hu, YB ;
Li, CM ;
Kulkarni, BA ;
Strobel, G ;
Lobkovsky, E ;
Torczynski, RM ;
Porco, JA .
ORGANIC LETTERS, 2001, 3 (11) :1649-1652
[9]   Molecular angiogenesis [J].
Klagsbrun, M ;
Moses, MA .
CHEMISTRY & BIOLOGY, 1999, 6 (08) :R217-R224
[10]   Torreyanic acid: A selectively cytotoxic quinone dimer from the endophytic fungus Pestalotiopsis microspora [J].
Lee, JC ;
Strobel, GA ;
Lobkovsky, E ;
Clardy, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3232-3233